1-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acid → Tyrosine, N-[[1-cyclohexyl-2-(3-furanyl)-1H-benzimidazol-5-yl]carbonyl]-3,5-difluoro-

HRID 1007716Notes

Reaction equation

HRID 1007716 reaction equation
Cl.C[O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([OH:15])=[C:10]([F:16])[CH:9]=1)[NH2:6].[CH:18]1([N:24]2[C:28]3[CH:29]=[CH:30][C:31]([C:33](O)=[O:34])=[CH:32][C:27]=3[N:26]=[C:25]2[C:36]2[CH:40]=[CH:39][O:38][CH:37]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>>[CH:18]1([N:24]2[C:28]3[CH:29]=[CH:30][C:31]([C:33]([NH:6][CH:5]([CH2:7][C:8]4[CH:13]=[C:12]([F:14])[C:11]([OH:15])=[C:10]([F:16])[CH:9]=4)[C:4]([OH:3])=[O:17])=[O:34])=[CH:32][C:27]=3[N:26]=[C:25]2[C:36]2[CH:40]=[CH:39][O:38][CH:37]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

3

Reactant 2

HCID 4911131-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acidHCID 69315745Racemic 3,5-difluorotyrosine methyl ester hydrochloride

Product 1

HCID 490790Tyrosine, N-[[1-cyclohexyl-2-(3-furanyl)-1H-benzimidazol-5-yl]carbonyl]-3,5-difluoro-

Procedure

Racemic 3,5-difluorotyrosine methyl ester hydrochloride (example 119) was coupled to the carboxylic acid of example 2 in the usual manner and saponified to give the title compound of example 123.

Sources & evidence

ORD record
ord-770c6badce1042c78764d82815f4f1d4
Source dataset
uspto-grants-2004_09
Patent number
US06794404B2

Reaction notes

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